Raines played the first 10 seasons of his career with the Expos, where he participated in seven consecutive All-Star games. Raines also played for the Chicago White Sox, New York Yankees, Oakland As and Baltimore Orioles. He returned for a final season with Montreal in 2001.

Late last season, Raines was traded to the Orioles, joining his son, Tim Jr., on the roster. The Raines became only the second father-son team to play with the same major league team, following Ken Griffey and Ken Griffey Jr. in Seattle.